Identification of essential oil components of Marrubium thessalum Boiss. & Heldr., growing wild in Greece

The essential oil of the Greek endemic species Marrubium thessalum Boiss. & Heldr. (Lamiaceae) was obtained by the hydrodistillation of its aerial parts during the flowering stage. The composition of the oil was analysed by GC and GC-MS. Thirty compounds were identified. The oil was devoid of monoterpenes, while sesquiterpenes constituted the major fraction. The main components of the oil were caryophyllene oxide (21.7%), β-caryophyllene (17.6%), germacrene D (15.3%), β-bisabolene (12.6%) and trans-β-farnesene (8.1%).     

Variation in the volatile constituents of Artemisia annua var. CIM-Arogya during plant ontogeny

The essential oils yield and composition of the aerial parts of A. annua var. CIM-Arogya grown in Uttarakhand, India were analyzed and compared by capillary GC and GC-MS at different stages of development. The analysis led to the identification of 81 constituents forming 91.0%-97.1% of the essential oils compositions. The essential oil content of the aerial parts was found to vary from 0.3% to 0.7% at different stages of growth. A. annua crop harvested at full flowering and seed setting stage gave higher yield of essential oil (0.6%, 0.7%) than that harvested at pre flowering (0.5%), late vegetative (0.4%, 0.5%), mid vegetative (0.4%, 0.4%) and early vegetative stages (0.3%, 0.3%). The essential oils at different stages of growth showed monoterpenoids (38.5%-72.0%) and sesquiterpenoids (22.2%-48.2%) as major grouped constituents. The major constituents identified were camphor (22.8%-42.6%), 1,8-cineole (3.7%-8.4%), linalool (<0.1%-11.9%), beta-caryophyllene (2.0%-9.2%), (E)-beta-farnesene (1.3%-8.5%), germacrene D (0.5%-7.3%) and 1-epi-cubenol (0.7%-5.2%) in essential oil samples collected at different crop stages.     

Chemical composition of the essential oil from the flowering aerial parts of Bupleurum hamiltonii Balak from Uttarakhand, India

The essential oil from the flowering aerial parts of Bupleurum hamiltonii Balak syn. Bupleurum tenue family Apiaceae (Umbellifereae) was obtained by steam distillation and analysed by a combination of GC (RI) and GC-MS. The chemical composition of the isolated oil is reported here for the first time. Twenty-seven compounds were identified, which represent 92.7% of the total oil. The chemical composition of the isolated oil was characterised by a high proportion of sesquiterpene hydrocarbons (61.9%), among which germacrene-D (17.8%), trans-β-farnesene (14.7%) and β-caryophyllene (13.1%) were the predominant compounds. The monoterpene hydrocarbons (16.6%) represented the second major fraction of the same oil followed by the oxygenated sesquiterpenes (7.9%).     

Essential Oil Composition of <Emphasis Type="Italic">Nepeta involucrata</Emphasis> from Iran

The essential oil of Nepeta involucrata (Bunge) Bornm. (Lamiaceae) obtained by hydrodistillation from the aerial parts during the flowering stage was analyzed by GC and GC-MS. Forty-eight compounds representing 97.2% of total oil were identified. The main compounds of the oil were 1,8-cineol (23.1%), germacrene-D (15.1%), and β-pinene (12.2%). No traces of nepetalactone isomers were found as oil constituents. __________ Published in Khimiya Prirodnykh Soedinenii, No. 6, pp. 562–564, November–December, 2005.     

Essential oil variation of Salvia officinalis aerial parts during its phenological cycle

In this paper the variation in the quantity and quality of the essential oil of Salvia officinalis during its life cycle stages is reported. The oils were obtained by hydrodistillation of air-dried samples. The yield of essential oil (w/w %) in different stages was in the order: floral budding (0.9%) > vegetative (0.7%) > flowering (0.5%) > immature fruit (0.4%) > ripen fruit (0.2%). The essential oils were analyzed by GC and GC-MS. In total, 36, 41, 40, 38, and 41 constituents were identified and quantified in the subsequent stages, respectively. Oxygenated monoterpenes were the main group of compounds in the fruiting set (56.9%), vegetative (48.5%), flowering (47.7%), and floral budding (45.3%) stage. 1,8-cineole as one of the major constituents of all samples was lower in the vegetative stage and gradually increased in subsequent harvesting times to reach a maximum in flowering and then decreased in the fruiting set. In contrast, the globulol content was higher in the first stage and decreased drastically during fruit maturation. Published in Khimiya Prirodnykh Soedinenii, No. 1, pp. 16–19, January–February, 2006.     

Seasonal variations of volatile constituents of Hemizygia bracteosa (Benth.) Briq. aerial parts from Benin

Essential oils from fresh aerial parts of Hemizygia bracteosa (Benth.) Briq. were extracted by steam distillation. The oil yield from plants collected during the hot season (February) and during the cold season (August) were 0.12 ± 0.01% and 0.25 ± 0.02%, respectively. GC/FID and GC/MS analyses allowed us to identify a total of 65 compounds, representing 97% of the hydrodistillate. The main components of the oil from the hot period were (E)-β-farnesene (64 ± 0.04%), β-elemene (7.4 ± 0.05%), trans-nerolidol (6.2 ± 0.04%), and α-muurolene (2.7 ± 0.03%). The essential oil from the cold season was characterized by the presence, as major compounds, of (E)-β-farnesene (67 ± 0.04%) along with β-caryophyllene (3.6 ± 0.06%), β-elemene (3.3 ± 0.05%), 7-epi-α-selinene (3.1 ± 0.01%) and p-cymene (2.5 ± 0.04%). This is the first report of these components in the essential oil of Hemizygia bracteosa (Benth.) Briq.     

Chemical composition and insecticidal activity against Sitophilus zeamais of the essential oils derived from Artemisia giraldii and Artemisia subdigitata

The aim of this research was to determine the chemical composition and insecticidal activity of the essential oils derived from flowering aerial parts of Artemisia giraldii Pamp. and A. subdigitata Mattf. (Family: Asteraceae) against the maize weevil (Sitophilus zeamais Motsch.). Essential oils of aerial parts of A. giraldii and A. subdigitata were obtained from hydrodistillation and investigated by GC and GC-MS. A total of 48 and 33 components of the essential oils of A. giraldii and A. subdigitata were identified, respectively. The principal compounds in A. giraldii essential oil were β-pinene (13.18%), iso-elemicin (10.08%), germacrene D (5.68%), 4-terpineol (5.43%) and (Z)-β-ocimene (5.06%). 1,8-Cineole (12.26%) and α-curcumene (10.77%) were the two main components of the essential oil of A. subdigitata, followed by β-pinene (7.38%), borneol (6.23%) and eugenol (5.87%). The essential oils of A. giraldii and A. subdigitata possessed fumigant toxicity against the maize weevils with LC50 values of 6.29 and 17.01 mg/L air, respectively. The two essential oils of A. giraldii and A. subdigitata also exhibited contact toxicity against S. zeamais adults with LD50 values of 40.51 and 76.34 μg/adult, respectively. The results indicated that the two essential oils show potential in terms of fumigant and contact toxicity against grain storage insects.     

Volatile constituents of Origanum vulgare L., 'thymol' chemotype: variability in North India during plant ontogeny

Essential oils derived from six different phenophases, namely early vegetative stage, late vegetative stage, early flowering stage, full flowering stage (FFS), late flowering stage and seed shattering stage of Origanum vulgare L. grown in Kumaon region of Uttarakhand, India were investigated by GC and GC-MS. A total of 38 constituents, representing 97.4-99.7% of the total oil composition, were identified. Major components of oils were thymol (40.9-63.4%), p-cymene, (5.1-25.9%), γ-terpinene (1.4-20.1%), bicyclogermacrene (0.2-6.1%), terpinen-4-ol (3.5-5.9%), α-pinene (1.6-3.1%), 1-octen-3-ol (1.4-2.7%), α-terpinene (1.0-2.2%), carvacrol (<0.1-2.1%), β-caryophyllene (0.5-2.0%) and β-myrcene (1.2-1.9%). Thymol, terpinen-4-ol, 3-octanol, α-pinene, β-pinene, 1,8-cineole, α-cubebene and (E)-β-ocimene were observed to be higher during FFS. The study showed that plant stage had a significant effect on the essential oil content and composition of O. vulgare grown in the hilly tracks of Northern India.     

Chemical composition of Silene morganae Freyn volatile oil

The essential oil composition of flowering aerial parts of Iranian Silene morganae Freyn (Caryophyllaceae) was analysed for the first time using gas chromatography and gas chromatography–mass spectrometry. Thirty-one compounds consisting of 90.3% of the volatile oil were detected. The major constituents were benzaldehyde (11.6%), (Z)-3-hexenyl acetate (9.6%), (E)-β-ocimene (8.2%) and linalool (7.4%). Terpenoids (43.5%), particularly monoterpene hydrocarbons (24.2%), had the highest contribution in S. morganae Freyn flowering aerial parts oil.     

Chemical Composition of the Essential Oil of <Emphasis Type="Italic">Salvia macilenta</Emphasis> from Iran

The hydrodistilled essential oil composition from the aerial parts of Salvia macilenta (Lamiaceae) from Iran was analyzed by GC and GC-MS. The oil analysis confirmed the characterization of thirty-one compounds, accounting for 99.4% of the total oil. Analysis of the oil showed that the oil of S. macilenta was rich in monoterpene hydrocarbons with a-pinene (60%) as the main component followed by γ-elemene (6.1%), thymol (5.2%), elemol (4.7%), and β-caryophyllene (4.1%).__________Published in Khimiya Prirodnykh Soedinenii, No. 2, pp. 136–137, March–April, 2005.     

Volatile constituents of Festuca nigrescens, Phleum alpinum and Poa alpina from N. W. Italian Alpine pastures

The composition of the volatile fractions of three important grasses from sub-alpine N.W. Italian pastures, namely Festuca nigrescens Lam. non Gaudin (chewing fescue), Phleum alpinum L. (alpine timothy) and Poa alpina L. (alpine bluegrass) was investigated. The fresh aerial parts were collected at the flowering stage during the summer season. The volatile oils obtained from green tissues by steam distillation in a Clevenger-type apparatus, were analyzed by GC/FID and GC/MS. The oil yield was 0.04 +/- 0.01% weight/fresh weight bases for each of the investigated species. Several classes of compounds were found in the volatile fractions, including aldehydes, alcohols, acids, hydrocarbons, esters, ketones, terpenes, and phenolics. Qualitative and quantitative differences were observed.     

Chemical constituents of the essential oil from aerial parts and fruit of Anisosciadium orientale

The essential oils from aerial parts and fruits of Anisosciadium orientale DC. growing wild in Iran were obtained by hydrodistillation and analyzed by GC and GC/MS. Seventy-one compounds were identified in the fruit oil and fifteen in the oil from the aerial parts. The main oil components of the fruits and aerial parts were myristicin (33.5%-33.7%), alpha-terpinolene (22%-25.8%) and limonene (19.5%-19.7%). Some compounds, such as geranyl butyrate and germacrene-D, were only detected in the fruit oil.     

Sesquiterpene-rich volatile constituents of Ipomoea obscura (L.) Ker-Gawl.

The hydro-distilled essential oil from flowering aerial parts of Ipomoea obscura (L.) Ker-Gawl. (Convolvulaceae) was investigated by using gas chromatography equipped with a flame ionisation detector GC-FID and gas chromatography coupled with a mass spectrometry (GC/MS). Forty-two components, representing 97.1% of the total oil, were identified. The major constituents of the essential oil were α-bulnesene (23.8%), α-humulene (13.7%) and seychellene (11.2%). The other minor constituents were α-guaiene (8.3%), β-caryophyllene (7.1%), γ-terpinene (4.2%), hexadecanoic acid (3.0%) and β-elemene (2.7%). The oil was found to be rich in sesquiterpene hydrocarbon type constituents (78.4%).     

Volatile constituents of Amomum maximum Roxb and Amomum microcarpum C. F. Liang & D. Fang: two Zingiberaceae grown in Vietnam

The chemical composition of essential oils obtained from the hydrodistillation of different parts of Amomum maximum Roxb and Amomum muricarpum C. F. Liang & D. Fang (Zingiberaceae) grown in Vietnam are reported. The analysis was performed by means of gas chromatography–flame ionisation detectoorand gas chromatography coupled with mass spectrometry. The major compounds identified in the oils of A. maximum were β-pinene (20.4–40.8%), α-pinene (6.8–15.0%), β-elemene (2.5–12.8%) and β-caryophyllene (2.3–10.3%). Moreover, β-phellandrene (11.6%) was present in the root oil. The main compound identified in all the oil samples of A. muricarpum was α-pinene (24.1–54.7%) and β-pinene (9.2–25.9%). In addition, limonene (7.4%) and δ-3-carene (9.4%) were present in the leaves and stem oils, respectively. However, while β-phellandrene (8.3%) could be seen prominent in the root oil, the fruits contained significant amount of zingiberene (6.3%). The largest amount of τ-muurolol (13.0%) was found in the flower oil.     

Toxicity of Rhododendron anthopogonoides essential oil and its constituent compounds towards Sitophilus zeamais

The screening of several Chinese medicinal plants for insecticidal principles showed that essential oil of Rhododendron anthopogonoides flowering aerial parts possessed significant toxicity against maize weevils, Sitophilus zeamais. A total of 37 components were identified in the essential oil and the main constituents of the essential oil were 4-phenyl-2-butanone (27.22%), nerolidol (8.08%), 1,4-cineole (7.85%), caryophyllene (7.63%) and γ-elemene (6.10%), followed by α-farnesene (4.40%) and spathulenol (4.19%). Repeated bioactivity-directed chromatographic separation on silica gel columns led us to isolate three compounds, namely 4-phenyl-2-butanone, 1,4-cineole, and nerolidol. 4-Phenyl-2-butanone shows pronounced contact toxicity against S. zeamais (LD?? = 6.98 mg/adult) and was more toxic than either 1,4-cineole or nerolidol (LD?? = 50.86 mg/adult and 29.30 mg/adult, respectively) against the maize weevils, while the crude essential oil had a LD?? value of 11.67 mg/adult. 4-Phenyl-2-butanone and 1,4-cineole also possessed strong fumigant toxicity against the adults of S. zeamais (LC?? = 3.80 mg/L and 21.43 mg/L) while the crude essential oil had a LC?? value of 9.66 mg/L.     

Seasonal variation of colchicine content in Colchicum brachyphyllum and Colchicum tunicatum (Colchicaceae)

As part of our continuing investigation of Jordanian Colchicum species, (-)-colchicine content in C. brachyphyllum Boiss. & Haussk. ex Boiss and Colchicum tunicatum Feinbr (Colchicaceae), growing wild in Jordan, was determined during different growth stages. Using external reference standard, a reverse-phase gradient photo-diode array high performance liquid chromatography (PDA-HPLC) method was adapted. Underground parts in both species and during different growth stages, always showed higher (-)-colchicine content than the above ground parts. In C. brachyphyllum total (-)-colchicine content of underground parts during flowering stage was found to be about 0.15% (wt/wt), while that of aerial parts was only about 0.04% (wt/wt). In C. tunicatum total (-)-colchicine content of underground parts was found to be 0.12% (wt/wt), and 0.13% (wt/wt) during flowering and vegetating stages, respectively, while that of aerial parts was only about 0.04% (wt/wt) and 0.02% (wt/wt), respectively. In C. tunicatum, stems, roots and unripe seeds are the main storages of (-)-colchicine at flowering, vegetating and seeding stages, respectively, while in C. brachyphyllum, corms are the main storage of (-)-colchicine at flowering and seeding stages.     

Variation of bioactive substances in Hypericum montbretii during plant growth

The present study was conducted to determine phenologic and morphogenetic variation of chlorogenic acid and flavonoids, as rutin, hyperoside, apigenin-7-O-glucoside, quercitrin, quercetin and viteksin content of Hypericum montbretii growing in Turkey. Wild growing plants were harvested at vegetative, floral budding, full flowering, fresh fruiting and mature fruiting stages and dissected into stem, leaf and reproductive tissues and assayed for bioactive compounds by HPLC method. Accumulation of rutin and quercetin was not detected in plant parts of H. montbretii during plant growth. Chlorogenic acid and hyperoside content in whole plant was decreased linearly with advancing of development stages and reached their highest level at vegetative stage. On the contrary, apigenin-7-O-glucoside, quercitrin and viteksin content in whole plant increased during the course of seasonal development and the highest level of those compounds was observed at the stage of full flowering. Leaves did not produce apigenin-7-O-glucoside, while viteksin was not detectable in stem and reproductive tissues. Depending on development stages, reproductive parts had the highest level of apigenin-7-O-glucoside and leaves produced major amount of chlorogenic acid, hyperoside and viteksin whereas accumulation of quercitrin was prevailed in stem tissue. Such kind of data could be useful for elucidation of the chemotaxonomical significance of these compounds and medicinal evaluation of this species.     

Essential oil composition of three species of Scutellaria from Turkey

The chemical compositions of the essential oils obtained by hydrodistillation from the aerial parts of Scutellaria diffusa, Scutellaria heterophylla and Scutellaria salviifolia were separately identified simultaneously by gas chromatography and gas chromatography-mass spectrometry. The main components were determined as hexadecanoic acid (30%) and caryophyllene oxide (9%) in the oil of S. diffusa. Germacrene D (21%), hexadecanoic acid (16%) and β-caryophyllene (13%) were found as major components in the oil of S. heterophylla. The main components of the oil of S. salviifolia were germacrene D (40%), bicyclogermacrene (14%) and β-caryophyllene (11%). Overall, individually 63, 68 and 43 constituents were identified in the aerial parts of S. diffusa, S. heterophylla and S. salviifolia essential oils representing 92.1%, 89.9% and 90% of the total, respectively.     

Influence of growth phase on the essential oil composition and antimicrobial activities of Satureja hortensis

The variations in quantity and quality of essential oils (EOs) from the aerial parts of cultivated Satureja hortensis were determined at different stages of harvesting. The EOs of air-dried samples were obtained by hydrodistillation and analyzed by gas chromatography/mass spectrometry (GC/MS). The antimicrobial activity of the EOs was investigated by broth microdilution methods. The amount of EOs (w/w, %) were 2.3, 2.5, 2.0, and 1.8% at floral budding, full flowering, immature fruit, and ripened fruit stages, respectively. gamma-Terpinene was the major compound of the EO at all developmental stages, except the ripened fruit stage when it was replaced by carvacrol (46.4%). The EOs exhibited strong antibacterial activities against the tested bacteria. Moreover, the EOs either inhibited or killed the examined yeasts at concentrations ranging from 0.03-8.0 microL/mL. Considering the wide range of antimicrobial activities of the examined EOs, they might have potential to be used in the management of infective agents.     

Variability of essential oils of Betonica officinalis (Lamiaceae) from different wild populations in Kosovo

The aerial parts and roots of Betonica officinalis were collected from three localities characterized by different ecological conditions to study the natural variability of the chemical composition of the essential oils in this plant. The leaves and inflorescences were collected during the flowering time, whereas the roots were collected at the end of the vegetative period. The plant material was dried at room temperature. The essential oils were obtained by micro-steam hydrodistillation and analyzed using gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). Overall, 69 constituents were identified in all localities and plant parts. The main compositions of the leaves in all localities were alpha-pinene, 1-octen-3-ol, beta-bourbonene, (E)-caryophyllene and germacrene D. The essential oil of the inflorescences was characterized by these main constituents: alpha-pinene, (E)-caryophyllene and trans-beta-farnesene. In all localities, the percentages of alpha-pinene and (E)-caryophyllene were higher in the inflorescences than in the leaves, whereas nonane was the main constituent in the roots.